# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FO5970
_database_code_depnum_ccdc_archive 'CCDC 1497236'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 N6, 2(Cl)'
_chemical_formula_sum            'C22 H16 Cl2 N6'
_chemical_formula_weight         435.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6748(3)
_cell_length_b                   10.2522(3)
_cell_length_c                   16.7835(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.528(1)
_cell_angle_gamma                90
_cell_volume                     1953.12(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    13792
_cell_measurement_theta_min      1.79
_cell_measurement_theta_max      27.42

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7005
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13792
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.42
_reflns_number_total             4428
_reflns_number_gt                3737
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+1.9775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4428
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.48461(5) 1.13817(5) 0.33866(3) 0.02240(13) Uani 1 1 d . . .
Cl2 Cl 0.75842(5) 0.40464(5) 0.57029(3) 0.02252(13) Uani 1 1 d . . .
N1 N 0.26669(15) 0.63626(16) 0.22968(10) 0.0148(3) Uani 1 1 d . . .
N2 N 0.38359(15) 0.41026(17) 0.28816(11) 0.0166(4) Uani 1 1 d . . .
H1N2 H 0.422(3) 0.336(3) 0.3085(17) 0.038(8) Uiso 1 1 d . . .
N3 N 0.51600(15) 0.52155(16) 0.38712(11) 0.0176(4) Uani 1 1 d . . .
N4 N 0.63976(15) 0.64536(18) 0.48506(11) 0.0173(4) Uani 1 1 d . . .
H1N4 H 0.672(3) 0.570(3) 0.5090(18) 0.042(8) Uiso 1 1 d . . .
N5 N 0.54104(15) 0.87170(17) 0.41550(10) 0.0158(3) Uani 1 1 d . . .
H1N5 H 0.508(2) 0.947(3) 0.3908(17) 0.036(8) Uiso 1 1 d . . .
N6 N 0.40256(15) 0.76049(16) 0.31979(10) 0.0157(3) Uani 1 1 d . . .
C1 C 0.22570(18) 0.51679(19) 0.19263(12) 0.0154(4) Uani 1 1 d . . .
C2 C 0.12634(19) 0.5101(2) 0.12737(13) 0.0189(4) Uani 1 1 d . . .
H2 H 0.088(2) 0.589(2) 0.1080(14) 0.014(6) Uiso 1 1 d . . .
C3 C 0.0887(2) 0.3902(2) 0.09312(13) 0.0219(4) Uani 1 1 d . . .
H3 H 0.021(2) 0.384(2) 0.0470(15) 0.020(6) Uiso 1 1 d . . .
C4 C 0.1485(2) 0.2765(2) 0.12320(14) 0.0223(5) Uani 1 1 d . . .
H4 H 0.121(2) 0.195(3) 0.0982(15) 0.024(6) Uiso 1 1 d . . .
C5 C 0.24635(19) 0.2809(2) 0.18827(13) 0.0199(4) Uani 1 1 d . . .
H5 H 0.286(2) 0.204(3) 0.2102(15) 0.026(7) Uiso 1 1 d . . .
C6 C 0.28558(18) 0.4017(2) 0.22293(12) 0.0167(4) Uani 1 1 d . . .
C7 C 0.42414(18) 0.52299(19) 0.32305(12) 0.0156(4) Uani 1 1 d . . .
C8 C 0.55050(18) 0.6380(2) 0.41897(12) 0.0163(4) Uani 1 1 d . . .
C9 C 0.68550(18) 0.7628(2) 0.51936(12) 0.0172(4) Uani 1 1 d . . .
C10 C 0.77930(19) 0.7670(2) 0.58853(13) 0.0209(4) Uani 1 1 d . . .
H10 H 0.809(2) 0.690(3) 0.6107(15) 0.025(6) Uiso 1 1 d . . .
C11 C 0.8212(2) 0.8865(2) 0.62010(14) 0.0240(5) Uani 1 1 d . . .
H11 H 0.885(2) 0.890(3) 0.6680(16) 0.028(7) Uiso 1 1 d . . .
C12 C 0.77255(19) 1.0031(2) 0.58324(14) 0.0227(5) Uani 1 1 d . . .
H12 H 0.804(2) 1.086(3) 0.6064(17) 0.036(8) Uiso 1 1 d . . .
C13 C 0.68047(19) 1.0007(2) 0.51438(13) 0.0195(4) Uani 1 1 d . . .
H13 H 0.648(2) 1.081(2) 0.4908(15) 0.022(6) Uiso 1 1 d . . .
C14 C 0.63568(18) 0.8797(2) 0.48275(12) 0.0172(4) Uani 1 1 d . . .
C15 C 0.49518(17) 0.75903(19) 0.38340(12) 0.0154(4) Uani 1 1 d . . .
C16 C 0.36435(17) 0.6445(2) 0.29088(12) 0.0156(4) Uani 1 1 d . . .
C17 C 0.19605(17) 0.75240(19) 0.20339(12) 0.0157(4) Uani 1 1 d . . .
C18 C 0.21136(19) 0.8212(2) 0.13593(13) 0.0200(4) Uani 1 1 d . . .
H18 H 0.271(2) 0.794(2) 0.1083(14) 0.015(6) Uiso 1 1 d . . .
C19 C 0.1328(2) 0.9225(2) 0.10692(14) 0.0240(5) Uani 1 1 d . . .
H19 H 0.141(2) 0.968(2) 0.0559(16) 0.027(7) Uiso 1 1 d . . .
C20 C 0.04432(19) 0.9539(2) 0.14606(14) 0.0215(4) Uani 1 1 d . . .
H20 H -0.011(2) 1.021(3) 0.1243(16) 0.028(7) Uiso 1 1 d . . .
C21 C 0.03312(19) 0.8846(2) 0.21507(13) 0.0195(4) Uani 1 1 d . . .
H21 H -0.027(2) 0.906(2) 0.2397(16) 0.029(7) Uiso 1 1 d . . .
C22 C 0.10857(18) 0.7817(2) 0.24391(12) 0.0176(4) Uani 1 1 d . . .
H22 H 0.104(2) 0.730(3) 0.2887(16) 0.030(7) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.347(3) . ?
N1 C1 1.406(3) . ?
N1 C17 1.457(2) . ?
N2 C7 1.332(3) . ?
N2 C6 1.389(3) . ?
N2 H1N2 0.91(3) . ?
N3 C7 1.329(3) . ?
N3 C8 1.331(3) . ?
N4 C8 1.335(3) . ?
N4 C9 1.387(3) . ?
N4 H1N4 0.91(3) . ?
N5 C15 1.333(3) . ?
N5 C14 1.385(3) . ?
N5 H1N5 0.91(3) . ?
N6 C16 1.322(3) . ?
N6 C15 1.330(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.94(2) . ?
C3 C4 1.392(3) . ?
C3 H3 0.97(2) . ?
C4 C5 1.384(3) . ?
C4 H4 0.96(3) . ?
C5 C6 1.399(3) . ?
C5 H5 0.95(3) . ?
C7 C16 1.467(3) . ?
C8 C15 1.461(3) . ?
C9 C10 1.398(3) . ?
C9 C14 1.408(3) . ?
C10 C11 1.378(3) . ?
C10 H10 0.91(3) . ?
C11 C12 1.404(3) . ?
C11 H11 0.96(3) . ?
C12 C13 1.382(3) . ?
C12 H12 0.97(3) . ?
C13 C14 1.402(3) . ?
C13 H13 0.96(3) . ?
C17 C18 1.380(3) . ?
C17 C22 1.386(3) . ?
C18 C19 1.396(3) . ?
C18 H18 0.96(2) . ?
C19 C20 1.386(3) . ?
C19 H19 1.00(3) . ?
C20 C21 1.390(3) . ?
C20 H20 0.96(3) . ?
C21 C22 1.387(3) . ?
C21 H21 0.92(3) . ?
C22 H22 0.93(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C1 122.11(17) . . ?
C16 N1 C17 119.88(16) . . ?
C1 N1 C17 117.91(16) . . ?
C7 N2 C6 122.97(18) . . ?
C7 N2 H1N2 118.2(19) . . ?
C6 N2 H1N2 118.8(18) . . ?
C7 N3 C8 115.21(17) . . ?
C8 N4 C9 122.98(18) . . ?
C8 N4 H1N4 118.9(19) . . ?
C9 N4 H1N4 118.2(19) . . ?
C15 N5 C14 123.29(18) . . ?
C15 N5 H1N5 117.4(18) . . ?
C14 N5 H1N5 119.3(18) . . ?
C16 N6 C15 115.19(17) . . ?
C2 C1 C6 119.59(19) . . ?
C2 C1 N1 121.54(18) . . ?
C6 C1 N1 118.87(18) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 122.4(14) . . ?
C1 C2 H2 118.0(14) . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 120.4(14) . . ?
C4 C3 H3 118.9(14) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 120.6(15) . . ?
C3 C4 H4 118.7(15) . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 121.2(15) . . ?
C6 C5 H5 119.6(15) . . ?
N2 C6 C5 120.87(19) . . ?
N2 C6 C1 118.70(18) . . ?
C5 C6 C1 120.42(19) . . ?
N3 C7 N2 118.85(18) . . ?
N3 C7 C16 122.10(18) . . ?
N2 C7 C16 119.03(18) . . ?
N3 C8 N4 119.25(18) . . ?
N3 C8 C15 122.31(18) . . ?
N4 C8 C15 118.43(18) . . ?
N4 C9 C10 121.49(19) . . ?
N4 C9 C14 118.54(18) . . ?
C10 C9 C14 119.96(19) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 123.6(16) . . ?
C9 C10 H10 117.4(16) . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.2(16) . . ?
C12 C11 H11 119.7(16) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.8(17) . . ?
C11 C12 H12 119.6(17) . . ?
C12 C13 C14 118.7(2) . . ?
C12 C13 H13 119.0(15) . . ?
C14 C13 H13 122.2(15) . . ?
N5 C14 C13 121.11(19) . . ?
N5 C14 C9 118.35(18) . . ?
C13 C14 C9 120.54(19) . . ?
N6 C15 N5 119.27(18) . . ?
N6 C15 C8 122.44(18) . . ?
N5 C15 C8 118.29(18) . . ?
N6 C16 N1 119.26(18) . . ?
N6 C16 C7 122.54(18) . . ?
N1 C16 C7 118.20(18) . . ?
C18 C17 C22 122.91(19) . . ?
C18 C17 N1 119.54(18) . . ?
C22 C17 N1 117.30(17) . . ?
C17 C18 C19 117.76(19) . . ?
C17 C18 H18 119.7(14) . . ?
C19 C18 H18 122.4(14) . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19 122.1(15) . . ?
C18 C19 H19 117.2(15) . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 119.8(15) . . ?
C21 C20 H20 120.0(15) . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 120.8(16) . . ?
C20 C21 H21 118.9(16) . . ?
C17 C22 C21 118.33(19) . . ?
C17 C22 H22 117.4(16) . . ?
C21 C22 H22 124.2(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N2 Cl1 0.91(3) 2.17(3) 3.0697(18) 168(3) 1_545
N4 H1N4 Cl2 0.91(3) 2.12(3) 3.0214(19) 175(3) .
N5 H1N5 Cl1 0.91(3) 2.14(3) 3.0270(18) 163(2) .
C5 H5 Cl1 0.95(3) 2.85(3) 3.601(2) 136.7(19) 1_545
C13 H13 Cl1 0.96(3) 2.87(2) 3.572(2) 131.4(18) .
C22 H22 Cl2 0.93(3) 2.88(3) 3.677(2) 144(2) 3_666

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.060
